Crystal Structure and Hirshfeld Surface Analysis of ()-6-(4-hy-droxy-3-meth-oxy-styr-yl)-4,5-di-hydro-pyridazin-3(2)-one

Overview

Journal Acta Crystallogr E Crystallogr Commun

Date 2019 Nov 12

PMID 31709099

Citations 4

Authors

Said Daoui

Cemile Baydere

Fouad El Kalai

Rafik Saddik

Necmi Dege

Khalid Karrouchi

Noureddine Benchat

Affiliations

Soon will be listed here.

Abstract

In the title com-pound, CHNO, the dihydropyridazine ring (r.m.s. deviation = 0.166 Å) has a screw-boat conformation. The dihedral angle between its mean plane and the benzene ring is 0.77 (12)°. In the crystal, inter-molecular O-H⋯O hydrogen bonds generate (5) chains and N-H⋯O hydrogen bonds produce (8) motifs. These types of inter-actions lead to the formation of layers parallel to (12). The three-dimensional network is achieved by C-H⋯O inter-actions, including (8) motifs. Inter-molecular inter-actions were additionally investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots. The most significant contributions to the crystal packing are by H⋯H (43.3%), H⋯C/C⋯H (19.3%), H⋯O/H⋯O (22.6%), C⋯N/N⋯C (3.0%) and H⋯N/N⋯H (5.8%) contacts. C-H⋯π inter-actions and aromatic π-π stacking inter-actions are not observed.

Citing Articles

Crystal structure of ()-3-({6-[2-(4-chloro-phen-yl)ethen-yl]-3-oxo-2,3-di-hydro-pyridazin-4-yl}meth-yl)pyridin-1-ium chloride dihydrate.

Daoui S, Cinar E, Dege N, Benchat N, Saif E, Karrouchi K Acta Crystallogr E Crystallogr Commun. 2022; 78(Pt 4):458-462.

PMID: 35492268 PMC: 8983968. DOI: 10.1107/S2056989022003346.

Crystal structure and Hirshfeld surface analysis of 6-(()-2-{4-[2-(4-chloro-phen-yl)-2-oxoeth-oxy]phen-yl}ethen-yl)-4,5-di-hydro-pyridazin-3(2)-one.

Daoui S, Muwafaq I, Cinar E, Abudunia A, Dege N, Benchat N Acta Crystallogr E Crystallogr Commun. 2022; 78(Pt 1):8-11.

PMID: 35079414 PMC: 8739192. DOI: 10.1107/S205698902101238X.

Synthesis, spectroscopy, crystal structure, TGA/DTA study, DFT and molecular docking investigations of ()-4-(4-methylbenzyl)-6-styrylpyridazin-3()-one.

El Kalai F, Cinar E, Lai C, Daoui S, Chelfi T, Allali M J Mol Struct. 2020; 1228:129435.

PMID: 33071353 PMC: 7546970. DOI: 10.1016/j.molstruc.2020.129435.

Crystal structure, Hirshfeld surface analysis and DFT studies of 2-[5-(4-methyl-benz-yl)-6-oxo-3-phenyl-1,6-di-hydro-pyridazin-1-yl]acetic acid.

Daoui S, Baydere C, El Kalai F, Mahi L, Dege N, Karrouchi K Acta Crystallogr E Crystallogr Commun. 2019; 75(Pt 12):1925-1929.

PMID: 31871759 PMC: 6895937. DOI: 10.1107/S2056989019015317.

References

Karrouchi K, Ansar M, Radi S, Saadi M, El Ammari L . Crystal structure of N'-di-phenyl-methyl-idene-5-methyl-1H-pyrazole-3-carbo-hydrazide. Acta Crystallogr E Crystallogr Commun. 2015; 71(Pt 11):o890-1. PMC: 4645091. DOI: 10.1107/S2056989015020071. View

Wang T, Dong Y, Wang L, Xiang B, Chen Z, Qu L . Design, synthesis and structure-activity relationship studies of 6-phenyl-4,5-dihydro-3(2H)-pyridazinone derivatives as cardiotonic agents. Arzneimittelforschung. 2009; 58(11):569-73. DOI: 10.1055/s-0031-1296558. View

El Kalai F, Baydere C, Daoui S, Saddik R, Dege N, Karrouchi K . Crystal structure and Hirshfeld surface analysis of ethyl 2-[5-(3-chloro-benz-yl)-6-oxo-3-phenyl-1,6-di-hydro-pyridazin-1-yl]acetate. Acta Crystallogr E Crystallogr Commun. 2019; 75(Pt 6):892-895. PMC: 6658951. DOI: 10.1107/S2056989019007424. View

Sonmez M, Berber I, Akbas E . Synthesis, antibacterial and antifungal activity of some new pyridazinone metal complexes. Eur J Med Chem. 2005; 41(1):101-5. DOI: 10.1016/j.ejmech.2005.10.003. View

Daoui S, Cinar E, El Kalai F, Saddik R, Karrouchi K, Benchat N . Crystal structure and Hirshfeld surface analysis of 4-(4-methyl-benz-yl)-6-phenyl-pyridazin-3(2)-one. Acta Crystallogr E Crystallogr Commun. 2019; 75(Pt 9):1352-1356. PMC: 6727051. DOI: 10.1107/S2056989019011551. View

Daoui S, Faizi M, El Kalai F, Saddik R, Dege N, Karrouchi K . Crystal structure and the DFT and MEP study of 4-benzyl-2-[2-(4-fluoro-phen-yl)-2-oxoeth-yl]-6-phenyl-pyridazin-3(2)-one. Acta Crystallogr E Crystallogr Commun. 2019; 75(Pt 7):1030-1034. PMC: 6659327. DOI: 10.1107/S2056989019008557. View

Groom C, Bruno I, Lightfoot M, Ward S . The Cambridge Structural Database. Acta Crystallogr B Struct Sci Cryst Eng Mater. 2016; 72(Pt 2):171-9. PMC: 4822653. DOI: 10.1107/S2052520616003954. View

Partap S, Akhtar M, Yar M, Hassan M, Siddiqui A . Pyridazinone hybrids: Design, synthesis and evaluation as potential anticonvulsant agents. Bioorg Chem. 2018; 77:74-83. DOI: 10.1016/j.bioorg.2018.01.001. View

Siddiqui A, Mishra R, Shaharyar M, Husain A, Rashid M, Pal P . Triazole incorporated pyridazinones as a new class of antihypertensive agents: design, synthesis and in vivo screening. Bioorg Med Chem Lett. 2011; 21(3):1023-6. DOI: 10.1016/j.bmcl.2010.12.028. View

10.

Zhou G, Ting P, Aslanian R, Cao J, Kim D, Kuang R . SAR studies of pyridazinone derivatives as novel glucan synthase inhibitors. Bioorg Med Chem Lett. 2011; 21(10):2890-3. DOI: 10.1016/j.bmcl.2011.03.083. View

11.

Barberot C, Moniot A, Allart-Simon I, Malleret L, Yegorova T, Laronze-Cochard M . Synthesis and biological evaluation of pyridazinone derivatives as potential anti-inflammatory agents. Eur J Med Chem. 2018; 146:139-146. DOI: 10.1016/j.ejmech.2018.01.035. View

12.

Livermore D, Bethell R, Cammack N, Hancock A, Hann M, Green D . Synthesis and anti-HIV-1 activity of a series of imidazo[1,5-b]pyridazines. J Med Chem. 1993; 36(24):3784-94. DOI: 10.1021/jm00076a005. View

13.

Spek A . Structure validation in chemical crystallography. Acta Crystallogr D Biol Crystallogr. 2009; 65(Pt 2):148-55. PMC: 2631630. DOI: 10.1107/S090744490804362X. View

14.

Gokce M, Utku S, Kupeli E . Synthesis and analgesic and anti-inflammatory activities 6-substituted-3(2H)-pyridazinone-2-acetyl-2-(p-substituted/nonsubstituted benzal)hydrazone derivatives. Eur J Med Chem. 2009; 44(9):3760-4. DOI: 10.1016/j.ejmech.2009.04.048. View

15.

Akhtar W, Shaquiquzzaman M, Akhter M, Verma G, Khan M, Alam M . The therapeutic journey of pyridazinone. Eur J Med Chem. 2016; 123:256-281. DOI: 10.1016/j.ejmech.2016.07.061. View

16.

Asif M . A mini review on biological activities of pyridazinone derivatives as antiulcer, antisecretory, antihistamine and particularly against histamine H3R. Mini Rev Med Chem. 2014; 14(13):1093-103. DOI: 10.2174/1389557514666141127143133. View

17.

Tao M, Aimone L, Gruner J, Mathiasen J, Huang Z, Lyons J . Synthesis and structure-activity relationship of 5-pyridazin-3-one phenoxypiperidines as potent, selective histamine H(3) receptor inverse agonists. Bioorg Med Chem Lett. 2011; 22(2):1073-7. DOI: 10.1016/j.bmcl.2011.11.118. View